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Synthesis 1992; 1992(1/2): 174-178
DOI: 10.1055/s-1992-34161
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A Model Study Directed Towards a Practical Enantioselective Total Synthesis of (-)-Morphine

Tomas Hudlicky* , Christie H. Boros, Eric E. Boros
  • *Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA
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Publikationsdatum:
18. September 2002 (online)

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A tricyclic ring system 10 containing the stereogenic centers of the nonaromatic portion of morphine (1) has been prepared in eight steps from toluene by the combination of microbial oxidation and intramolecular Diels-Alder cycloaddition followed by a Cope rearrangement. Experimental and spectral data are provided for all key compounds and potential for a short synthesis of morphine is indicated.